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The Structure of the Ion Pairs Formed by the Radical Anion of [2.2] Paracyclophane and the Potassium Cation

✍ Scribed by Fabian Gerson; William B. Martin Jr.; Christoph Wydler

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
333 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The structure of the title ion pairs has been established by ESR. studies of the radical anion produced from 1,1,10,10,12,13,15,16‐octadeuterio[2.2]paracyclophane with potassium in tetrahydrofuran and 2‐methyltetrahydrofuran. The counter‐ion K⊕, which for steric reasons is forced to reside outside the framework of [2.2]paracyclophane, assumes a position above the centre of one benzene ring. Experimental support has been also obtained for the assignment of the coupling constants to those ring and methylene protons which are rendered non‐equivalent by the ion pairing.

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## Abstract 4,5,7,13,15,16‐Hexamethyl‐ **(3)** and 4,5,7,8,12,13,15,16‐octamethyl[2.2]paracyclophane **(4)** have been oxidized to their radical cations in solution under relatively mild conditions. Substantial hyperfine splittings in the ESR. spectra of **3⊕.** and **4⊕.** arise from the methyl pr